Birch Reduction

Mechanism of the Birch Reduction

Sample reactions

Li
EtOH, NH3, THF
Reflux, 60 min, 90%


Na
EtOH, NH3, THF
-78 °C, 10 min, 54%


Li
NH3, THF
-60 °C, , 100%


Na
NH3, THF
-78 to -45 °C, 2 h, 100%


Li, NH3
THF


Li
NH3, t-BuOH
-78 °C, 6 h, 97%


Li
NH3, t-BuOH
-68 °C, 3 h, 97%


Na
NH3, t-BuOH, THF
-78 to -33 °C, 45 min, 100%


Li
EtOH, NH3, THF
-33 °C, 3.5 h, 83%



K
NH3, t-BuOH, THF
-78 °C, , 98%


Na
i-PrOH, NH3, THF
-78 °C, 4 h, 97%
"Acidic quench."


Li
Et2O, NH3
98%


Li
NH3, t-BuOH, THF
-75 to -55 °C, 5.5 h, 90%


Na
EtOH, NH3
-78 °C


AcCl, Li
THF
-85 °C to RT, 8 h



Li
NH3, THF
-33 °C, 2.5 h, 75%


Li
EtOH, NH3, THF
-78 to -33 °C


Na
EtOH, NH3, THF
-34 °C, , 95%


Na
EtOH
Reflux


H2O, HCl, Li, BrCH2CO2t-Bu
NH3, t-BuOH, THF
-40 °C to RT, 6 h, 90%


Na
NH3, t-BuOH, THF
-78 to -45 °C, 15 min, 82%
